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House vacation rentals in Downtown Chicago

Find and book unique houses on Airbnb

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Popular amenities for Downtown Chicago house rentals

House rentals with a pool

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.
Home in Glen Ellyn
4.8 out of 5 average rating, 10 reviews

Pardizes Suites

LeslieRating, 5 stars2 weeks ago
It was a gorgeous home, she knew we were coming for my husbands bday and she got us a bottle of wine and balloons. She was very helpful and responsive if we needed anything. Great place to stay!
Guest favorite
A swimming pool is seen surrounded by a white fence, with colorful pool floats inviting fun. Sunlight reflects off the clear blue water, and lush green trees provide a natural backdrop. A patterned mat lies at the edge, enhancing the relaxing atmosphere.
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars6 months ago
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.
A single-story house is set against a backdrop of trees, featuring a stone facade and a sloped roof. A winding driveway leads to a two-car garage on the right. Lush green grass surrounds the home, contributing to a serene environment.
Home in Lockport
4.55 out of 5 average rating, 11 reviews

Hidden GEM OASIS in Chicagoland

BesjanaRating, 5 stars1 month ago
Everything was great! The place was just as imagined.
A living room is presented with light wooden flooring and a soothing grey wall. Two red sofas are arranged for seating, facing a wall-mounted television. Natural light filters through two textured window shades, and a lamp stands beside the furnishings, adding to the room's cozy layout.
Home in Schaumburg
4.75 out of 5 average rating, 12 reviews

Spacious 3 Floor Townhome

Jocelyn DianeRating, 5 stars1 month ago
Super cool host, very flexible and kind. When I come back im definitely going thru him again!
Superhost
A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars3 weeks ago
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!
Guest favorite
A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.
Home in Bloomingdale
4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.
Guest favorite
Home in Schaumburg
4.92 out of 5 average rating, 26 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

SarahRating, 5 stars5 days ago
We stayed here while our floors were being refinished and Marzena’s Oasis did not disappoint! You can tell she takes great pride in her listing; everything was as described and more. The home was very clean with plenty of linens, dishes, and kitchen/pantry supplies. My kids left more crumbs on the floor than usual during breakfast one day…I could not find a broom so I messaged Marzena. She dropped off a stick vacuum AND some delicious treats. Above and beyond to make us feel welcome and comfortable. Thank you for a home away from home!
A spacious living area features a large projector screen displaying a vibrant image. Comfortable seating surrounds a modern electric fireplace, while a potted plant and decorative artwork add subtle touches to the space. Natural light is invited through nearby sliding glass doors.
Home in Chicago
New place to stay

LUXURY - Movie Theater + Spa House

JuanRating, 5 stars3 days ago
Great getaway place to stay at. Beautiful patio area as well!

Weekly house rentals

Superhost
A modern living area is showcased with a cozy sectional couch in a warm orange hue. A flat-screen TV is mounted above a sleek fireplace, framed by dark paneling. Two round mirrors and side tables with lamps are positioned on either side, enhancing the space's contemporary design.
Home in Chicago
5 out of 5 average rating, 8 reviews

The Modern Muse of Chicago! Close to everything!

CameronRating, 5 stars2 months ago
This Airbnb exceeded our expectations in every way! It was even better in person—much more spacious than we anticipated. The home was stocked with thoughtful amenities, especially in the kitchen, which made our stay incredibly convenient. The outdoor seating area was a great place to relax, and we loved the location. It truly felt like a home away from home, with everything we could possibly need already there. The host was also very attentive and accommodating, making the experience even better. We would definitely stay here again!
Superhost
A modern living area features large windows providing ample natural light and stunning city views. A round coffee table is set in the center, surrounded by a sectional sofa with soft cushions. Additionally, a workspace is visible, equipped with a desk and ergonomic chair.
Home in Oak Park
4.78 out of 5 average rating, 87 reviews

Rooftop Access with Views and Gym - LCP Collection

CynthiaRating, 5 stars1 week ago
Great place in a great location. Would definitely book again!
Superhost
A modern kitchen featuring stainless steel appliances, including a refrigerator and gas range. A spacious island with white marble countertop is surrounded by light-colored chairs. Above, stylish pendant lights provide ample illumination, while the open layout invites natural light from adjacent glass doors.
Home in Chicago
4.96 out of 5 average rating, 74 reviews

NEW! 3BR/2.5B Duplex in Noble Sq

AdamRating, 5 stars1 month ago
Host is very accommodating and responsive. The place is nice and was in a great location. Only a short 10 minute drive that was a straight shot to Michigan Ave. The only thing we felt was slightly misleading was that we were under the impression that the 3rd bedroom with a couch was able to pull out and convert into a bed. Unfortunately, that wasn’t the case, so we ended up leveraging an air mattress we had packed as a contingency. Overall, we had an enjoyable stay and would recommend.
Superhost
A modern kitchen features dark wood cabinetry paired with light granite countertops. Stainless steel appliances, including a refrigerator and oven, are enhanced by a stylish backsplash. A dining area with a square table and tall chairs is complemented by bar seating at the island.
Home in Chicago
4.95 out of 5 average rating, 40 reviews

Floresitas Oasis, your home in Chicago

KelvinRating, 5 stars3 days ago
Lizbeth’s place was a great stay! It was cozy, clean, and had more than enough space for me and my three friends. While it was a little farther from the city center than I initially expected, the neighborhood made up for it with tons of great restaurants nearby—there was always something good to eat just around the corner. Lizbeth was also a fantastic host—very friendly and super responsive whenever we had questions. Would definitely recommend her place to anyone visiting the area!
Superhost
A two-story brick home features a welcoming front porch with a stoop and entrance framed by tall windows. Lush greenery and vibrant flower beds add color to the exterior, enhancing the inviting presence of the residence.
Home in Chicago
4.95 out of 5 average rating, 19 reviews

Big house in the BEST Location!

AbhishekRating, 5 stars1 week ago
It was as pictured and suited our needs. Clean and well organized. When we reached out we were responded to promptly and thoroughly. The location is good and walkable. If planning to go to Navy Pier or the Miracle Mile to go shopping (or something in that general area of Chicago), expect about a 40 - 60 min drive.
Superhost
A modern living area is highlighted by a sectional sofa adorned with decorative cushions. Natural light enters through multiple windows, complementing the sleek design. A flat-screen television is mounted on the patterned wall, and a soft rug covers the polished hardwood floor.
Home in Chicago
4.83 out of 5 average rating, 70 reviews

Brand New Spacious Duplex

LillianRating, 5 stars2 days ago
I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.
Superhost
A stylish living area features a tufted brown leather sofa adorned with decorative pillows. An abstract wall art piece in muted tones hangs above a low coffee table. Warm wood flooring contrasts with dark wall panels, while a staircase and additional seating area are visible in the background.
Home in Chicago
5 out of 5 average rating, 23 reviews

Villa Noir Chicago Victorian 7 min to downtown

EddieRating, 5 stars1 week ago
Great place. Great communication. Perfect for what we needed. Great house. Great neighborhood, right outside of downtown.
Superhost
A spacious living area features high ceilings with detailed molding and a large decorative light fixture. Comfortable seating options include a plush sectional and a soft area rug. Natural light floods the room through large windows, illuminating the warm color palette of the walls.
Home in Chicago
4.81 out of 5 average rating, 43 reviews

Lux Home Chicago 7mins Downtown

TedRating, 5 stars3 days ago
Larry’s place was a perfect home base for our family celebrating UChicago convocation. Only about 2 miles from campus. Very easy drive. Nice house in a quiet neighborhood. Just what we needed.

Private house rentals

Superhost
A spacious living area features a large sectional sofa adorned with colorful throw pillows. Sunlight streams through multiple windows, illuminating a light-colored rug. A ceiling fan is positioned above, and a modern television mounted on the wall complements the neutral tones.
Home in Chicago
4.91 out of 5 average rating, 46 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

ChepeRating, 5 stars2 weeks ago
Very comfortable place and nice and very responsive host! Definitely recommend this stay!
Superhost
Home in Chicago
4.64 out of 5 average rating, 14 reviews

A home away from home.

NicoleRating, 5 stars9 months ago
Me my freinds and family enjoyed our stay. The host was very quick to respond to any concerns. The home was clean and spacious. The decor was nice to take pictures. I liked that it had a bathroom downstairs for easy assess. We will come back when we visit Chicago again. Thanks you guy you were awesome.
Guest favorite
The exterior of a restored Victorian house is presented, featuring a striking red front door and large windows that invite natural light. A welcoming porch is adorned with seating, surrounded by meticulously landscaped greenery and plants, creating an engaging atmosphere.
Home in Chicago
4.98 out of 5 average rating, 95 reviews

Victorian House in Heart of Rogers Park

KrystleRating, 5 stars5 days ago
This was my second stay at this location, and our family had the BEST time! We stayed for five days. The house is very immaculate; not a trace of dirt or dust anywhere. Like last time, we were left with some yummy snacks and treats upon arrival. Kris & Daniel also went above and beyond when we wanted to go to the beach - they personally came right over and got some beach chairs, towels, and an umbrella from the basement for us. The house is very comfortable with high-tech smart devices and we were nice and cool despite the heat (and nice and warm when it got chilly later in our visit). Our last day, I accidentally pulled down a curtain rod when opening the drapes, and Kris & Daniel could not have been more gracious about it. Great house and great hosts! Thank you!
Top guest favorite
The exterior of a historic two-story building is presented, featuring a contrasting mix of white and blue facades. A striking red door serves as the focal point, framed by elegant architectural details. A wrought iron fence surrounds the property, enhancing its charming curb appeal.
Home in Chicago
5 out of 5 average rating, 73 reviews

Windy City White House (3br/2ba) *New Listing*

SamanthaRating, 5 stars4 days ago
Beautiful place! Very clean! The host was very responsive. The kitchen was stocked with tea, coffee and extras. I love that they had a tea kettle. The rental had everything we needed, extra bedding and towels. We arrived to a basket of snacks and drinks 😊. Comfy beds and sofa in the sitting room. Lots of room for a family of 4. It is an upstairs unit so stairs to climb. Location was ok.
Superhost
An open-concept kitchen and living area features a modern design, highlighted by sleek cabinetry and a spacious island with seating. Natural light fills the room, accentuating the contemporary fixtures and appliances. A comfortable couch is positioned in the inviting living space, creating a perfect gathering spot.
Home in Chicago
4.89 out of 5 average rating, 28 reviews

Executive Contemporary Duplex

WaljimaRating, 5 stars1 week ago
My family and I enjoyed staying here. I was born and raised in Chicago just 4 blocks from this Airbnb! It was such a great experience to be back in my old neighborhood. Olusesan is a phenomenal host! I highly recommend this place.
Guest favorite
A cozy living area features a comfortable light-colored sectional sofa and a plush armchair facing a stone fireplace. Light wood flooring is complemented by a decorative area rug. A floor lamp and wall-mounted shelves add to the inviting decor, while natural light streams in through the entrance.
Home in Chicago
4.91 out of 5 average rating, 77 reviews

Beverly House

StarrRating, 5 stars3 days ago
The home was cozy and super convenient for what we needed. The backyard was so nice to get some outside time with the kids and we walked to the park up the street a couple of times. The kitchen had everything we needed. Melissa was very helpful in sharing what to know before getting there and a printed manual of facts and tips about the home, the area and some games to play, too. We would book again!
Guest favorite
A stylish living space showcases modern furnishings, including a vibrant rug and contemporary seating areas. Natural light floods in, highlighting the elegant design that invites relaxation. Adjacent is a spacious rooftop terrace adorned with lounge furniture, offering expansive views of the skyline.
Home in Chicago
4.98 out of 5 average rating, 62 reviews

① Lux | Spa | Rooftop | Modern | 4 Mi to Downtown

DaisyRating, 5 stars3 days ago
Anita’s place was absolutely stunning and looked just like the photos. Extremely clean and very spacious. We hosted a 50th birthday brunch here and it was more than enough space and amenities to accommodate everyone. The rooftop was just amazing and a great addition to the place. Thank you Anita for letting us book your gorgeous home and we would love to book again and again! ⭐️⭐️⭐️⭐️⭐️
Superhost
Home in Chicago
4.86 out of 5 average rating, 78 reviews

Sophisticated Twnhm in Prestigious S. Lincoln Park

DinaRating, 5 stars2 weeks ago
We really enjoyed Kyriako’s space! My husband, two toddlers, and I spent the long weekend in Chicago. This space had everything we needed for a comfortable stay. The location was great and we had access to tons of activities for family fun. We would definitely recommend this space for a family trip to Chicago!

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